Middletown, NY

Travel Guide

A lake surrounded by autumn-colored trees reflecting on the water.
A large steel bridge spanning a river, surrounded by trees and buildings.
A steel arch bridge over a river with surrounding trees and buildings.
A calm lake at sunset with trees and grass along the shore.
A statue of a man in a hat holding a lantern, standing on a green pedestal.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
$113 nightly
The price is $134 total per night from Nov 22 to Nov 23
$134 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$100 nightly
The price is $118 total per night from Nov 9 to Nov 10
$118 total
Nov 9 - Nov 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,253 reviews)
"I stayed here twice. I thought the hotel was amazing. The price was reasonable; it was very clean, and there was plenty of parking. I really liked my king-size bed; the staff was very friendly. The breakfast was awesome. I was expecting it to be some form of continental breakfast, but it was actually ..."

Reviewed on Nov 5, 2026

Sleep Inn & Suites Middletown - Goshen
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing Middletown NY
$105 nightly
The price is $125 total per night from Nov 19 to Nov 20
$125 total
Nov 19 - Nov 20
Total with taxes and fees
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Courtyard by Marriott Middletown Goshen
See all 1,497 properties in Middletown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Sun Retreats Birchwood Acres

Sun Retreats Birchwood Acres

2.5 out of 5
85 Martinfeld Rd Greenfield Park NY
Stay at this cabin in Greenfield Park. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions East Pond and Sullivan County Dramatic Workshop ...
10/10 Exceptional! (4 reviews)
"Good property, very clean and amazing staff. The only issue was the kids water park wasn’t working what made the kids very frustrated."

Reviewed on Oct 24, 2026

Sun Retreats Birchwood Acres
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush NY
Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Ellenville Fault Ice Caves and VerKeerderkill Falls are located nearby.
10/10 Exceptional! (26 reviews)
"The location was very impressive, the pictures don’t do it justice. Once you arrive, especially at night, the place looks majestic. It was the perfect calming and relaxing atmosphere it suggested. We took a beautiful walk along a peaceful trail surrounded by nature, and it was exactly what we needed. ..."

Reviewed on Nov 1, 2026

TRANQUIL MOUNTAIN SOLITUDE
Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking

Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking

vernon NJ
Book a stay at this golf cabin in Vernon. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mountain Creek Ski Resort and Crystal ...
Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking
See all properties in Middletown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Middletown attractions

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)
Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.
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Frequently asked questions

Is Middletown worth visiting?
Middletown is worth visiting for its diverse dining scene, offering both Italian and Asian cuisine. Travelers can also find entertainment at the Orange County Fair Speedway and enjoy shopping at the Galleria at Crystal Run, providing a variety of experiences.
When is the best time to visit Middletown?
The best time to visit Middletown is from May through September, when the climate is generally pleasant. For fewer crowds and better value, the quieter months of December through March are a good option, offering cooler temperatures and the possibility of snow.
What is Middletown known for?
Middletown is known for the Orange County Fair Speedway, a hub for entertainment, and the Galleria at Crystal Run, offering various shopping experiences. Travelers can also visit the Orange County Fairgrounds for events. The city features a strong Italian food culture, providing diverse dining options to explore.
What is a good itinerary length for Middletown?
A good itinerary length for Middletown is two to three days to experience key highlights like the Orange County Fair Speedway, Galleria at Crystal Run, and Orange County Fairgrounds. An extended stay of four to five days allows for more relaxed exploration and enjoying the local Italian, Asian, and North American dining options.
What are the top things to do in and around Middletown?
Middletown provides a mix of entertainment, shopping, and local landmarks to explore:


How do I plan a trip to Middletown?
To plan your trip to Middletown, book flights, hotels, and rental cars in advance. Consider activities like visiting Orange County Fair Speedway or Orange County Fairgrounds. Remember to pair outdoor plans with indoor backups for weather flexibility. You can also explore dining at local Italian, Asian, or North American restaurants. Search for places to stay and things to do on Expedia.
What cuisines can you find in Middletown?
In Middletown, travelers can find New American cuisine, featuring dishes like gourmet burgers, artisanal flatbreads, and creative small plates. You can also enjoy Italian favorites such as pasta and pizza, or Latin American options like tacos and burritos. The area also offers various coffee shops and cocktail bars.
Can I book a refundable hotel in Middletown?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middletown by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Middletown with Expedia?
Expedia makes it easier to plan your Middletown trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Middletown?
The best choice depends on your travel style. Hotels in Middletown can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Middletown trip on Expedia?
Once you've booked your Middletown trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Middletown trip?
Expedia offers customer support before, during, and after your Middletown trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Middletown?
If it's your first trip to Middletown, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Middletown hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Middletown hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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